Insurtech: Cowbell, Provider of Cyber Insurance for SMEs, to Enhance Underwriting Capabilities

Cowbell, the provider of cyber insurance for small and medium-sized enterprises (SMEs), announced it is bolstering its underwriting capabilities with new additions to its UK and US teams.

Claud Bilbao joins “as UK Director of Underwriting, reporting to Simon Hughes, General Manager for UK operations.” Matt Byrne joins “as Vice President of Tech E&O Underwriting, reporting to Caroline Thompson, Senior Vice President of Underwriting.”

Trent Cooksley, Co-founder, and Chief Operating Officer at Cowbell, said:

“We are dedicated to closing the insurability gap and making cyber insurance accessible to small to medium-sized businesses around the world. As seasoned underwriters with a wealth of experience across the cyber and technology insurance sector, Claud and Matt will help us deliver on this goal. They are valuable additions to our growing UK and US teams.”

Bilbao most recently “served as a Senior Underwriter at CNA, responsible for running the London Specialty Cyber and Technology portfolios on both their Company and Lloyd’s platforms.”

He played “a vital role in the successful development and execution of CNA’s London strategy. Bilbao was previously a US technology and cyber underwriter at CFC Underwriting, where he was focused on US West Coast and Silicon Valley technology startups and SMEs.”

Claud Bilbao, UK Director of Underwriting at Cowbell, said:

“I have seen firsthand how critical cyber insurance is for SMEs and large global enterprises. I am eager to bring my experience working with companies internationally to support Cowbell’s growing UK team.”

Byrne is also “a seasoned underwriter with over eight years of underwriting experience in Cyber and Professional Lines at traditional carriers and MGAs, supporting SMEs with up to multi-billion revenue risks.”

In addition to working on professional lines, Byrne has experience “working on traditional P&C lines supporting larger programs.” He is based “in the San Francisco Bay Area and focused on retail and wholesale relationships across the US.”

Matt Byrne, Vice President of Tech E&O Underwriting at Cowbell, said:

“I am thrilled to help the company continue innovating and delivering value to SMEs. I share Cowbell’s vision to close the SME insurability gap and am eager to use my skills to help drive Cowbell’s mission forward.”

These new hires “come amid Cowbell’s continued corporate growth, with the company recently announcing the appointment of Andrea Collins as its first CMO, opening a new technology center in Pune, India, and announcement of Simon Hughes as General Manager to lead the UK operations.”

As covered, Cowbell claims it is “a pioneer of Adaptive Cyber Insurance, a leader in providing small and medium-sized enterprises (SMEs) coverage adaptable to today’s and tomorrow’s threats and the advanced warning of cyber risk exposures.”

In its unique AI-based approach to risk selection and pricing, Cowbell’s continuous underwriting platform, “powered by Cowbell Factors, compresses the insurance process from submission to issue in less than 5 minutes.”

Cowbell is “backed by 20 prominent leading global (re)insurance partners and serves SMEs in 50 U.S. states and the District of Columbia.”

Founded in 2019, Cowbell is “based in the San Francisco Bay Area with employees across the U.S., Canada, India, and the U.K.”



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Disclosure Quest

Reg A - Form 1-A Filings Beta

Beta. Initial Form 1-A only. Target raise is the stated Amount to be Raised, totaled. Compared with the same dates one year earlier.

YTD: Jan 1, 2026 - Oct 26, 2026 vs Jan 1, 2025 - Oct 26, 2025

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Number of Filings131Prior 126 +4.0%
Target Raise, Total$3.40BPrior $3.54B -3.9%
This YTDYear priorChange
Filings 131 126 +4.0%
Target raise $3.40B $3.54B -3.9%

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